Aminosulfonylureas with herbicidal activity

ABSTRACT

This invention relates to aminosulfonylureas possessing a high herbicidal activity, a process for their preparation and their application to control control weeds in agriculture. Aminosulfonylureas of this invention have the following formula (I):                    
     wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are described in the specification.

This invention relates to aminosulfonylureas.

More in particular, this invention relates to aminosulfonylureaspossessing a high herbicidal activity, a process for their preparationand their application as herbicides for controlling weeds inagricultural cultures. Aminosulfonylureas with herbicidal activity have,among other things, been described in the U.S. Pat. Nos. 4,515,620,4,559,081, 4,592,776, 4,622,065 and 4,666,508. However, these productsturn out to have a very poor selectivity while generally being toxic tothe most important agricultural cultures.

The applicant has now discovered new aminosulfonylureas which have ahigher herbicidal activity against numerous weeds, exhibiting at thesame time a low phytotoxicity to one or more of the cultivations ofprime agricultural interest. Therefore, they have a higher cellselectivity.

The object of this invention are thus aminosulfonylureas of thefollowing general formula (I):

in which:

R represents a halogen atom such as chlorine, fluorine, bromine oriodine; an alkylic or haloalkylic linear or branched C₁-C₄ group; analkoxylic or haloalkoxylic linear or branched C₁-C₄ group;

N represents 0 or 1;

R₁ and R₂, equal or different from each other, represent an atom ofhydrogen; an alkylic or haloalkylic linear or branched C₁-C₄ group; analkoxylic or haloalkoxylic linear or branched C₁-C₄ group; or, jointly,an alkylenic or oxyalkylenic C₂-C₅ chain;

R₃ and R₄, equal or different from each other, represent an atom ofhydrogen; an alkylic or haloalkylic linear or branched C₁-C₄ group; analkoxyalkylic or haloalkoxyalkylic linear or branched C₃-C₆ group; analkenylic or haloalkenylic linear or branched C₃-C₆ group; an alkynylicor haloalkynylic linear or branched C₃-C₆ group;

R₅ and R₆, equal or different from each other, represent an atom ofhydrogen; a halogen atom such as chlorine, fluorine, bromine or iodine;an alkylic or haloalkylic linear or branched C₁-C₆ group; an alkylaminiclinear or branched C₁-C₆ group; a dialkylaminic linear or branched C₂-C₈group; a cycloalkylic or cycloalkoxylic C₃-C₆ group; a cycloalkylalkylicor cycloalkylalcoxylic C₄-C₇ group;

Z represents CH or N.

The aminosulfonylureas of the general formula (I) are endowed with highherbicidal activity. Specific examples of aminosulfonylureas having thegeneral formula (I) which are interesting for their herbicidal activityare:

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N,N-dimethyl-benzamide;

1-[(4,6-dimethoxypyrimidin-2-yl)-3-{[2-(1-pyrrolidinocarbonyl)phenyl]sulfamoyl}urea,

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-ethyl-N-methylbenzamide;

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-methylbenzamide;

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-ethylbenzamide;

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-methoxybenzamide;

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-methoxy-N-methylbenzamide;

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]benzamide;

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylmethylamino]-N,N-dimethylbenzamide;

N-cyclopropyl-2-[(4,6-dimethoxypyrimidin-2-yl) carbamoylsulfamoylamino]-benzamide;

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-(2,2,2-trifluoroethyl)benzamide;

4-chloro-6-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N,N-dimethylbenzamide;

3-chloro-6-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N,N-dimethylbenzamide;

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-5-fluoro-N,N-dimethylbenzamide;

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-6-fluoro-N,N-dimethylbenzamide;

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-5-methyl-N,N-dimethylbenzamide;

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-6-methyl-N,N-dimethylbenzamide;

N,N-dimethyl-2-[(4-methoxy-6-methylpyridin-2-yl)carbamoylsulfamoylamino]-benzamide;

N,N-dimethyl-2-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoylsulfamoylamino]-benzamide.

N,N-dimethyl-2-[(4,6-dimethylpyrimidin-2-yl) carbamoylsulfamoylamino]benzamide.

The aminosulfonylureas having the general formula (I) of the presentinvention have an acidic nature and can therefore form salts with basicsubstances such as, for example, alkaline metal and alkaline earthhydroxides, amines and other organic bases, and quaternary amine salts.

The aminosulfonylureas having the general formula (I) in their salifiedform also fall within the scope of this invention and thereforeconstitute a further object of the same.

A further object of this invention is a process for the preparation ofcompounds having the general formula (I). The compounds having thegeneral formula (I) may be obtained by a process including:

(a) reacting a heterocyclic amine having the general formula (II):

in which R₄, R₅, R₆, and Z have the meanings as described above, with ahalosulfonylisocyanate having the general formula (III):

X—SO₂—NCO  (III)

in which X represents a halogen atom such as, for instance, chlorine,fluorine, or bromine, preferably chlorine, in the presence of an inertorganic solvent, whereby a halosulfamoylurea of the following generalformula (IV) is obtained:

in which X, R₄, R₅, R₆, and Z have the meanings as described above;

(b) reacting of halosulfamoylurea having the general formula (IV)obtained in the step (a) with an aniline having the general formula (V):

in which R, R₁, R₂, and R₃ have the same meanings described above, inthe presence or absence of a base, preferably in the presence of a base,and of an inert organic solvent.

The inert organic solvents useful in the steps (a) and (b) of theprocess described above are aromatic hydrocarbons (such as for examplebenzene, toluene, xylene, etc.), chlorinated hydrocarbons (such as forexample, methylene chloride, chloroform, carbon tetrachloride,chlorobenzene etc.), and ethers (such as, for example, ethyl ether,dimethoxyethane, tetrahydrofurane, dioxane, etc.).

The bases useful in the step (b) of the process described above areorganic bases, preferably aliphatic amines such as, for example,triethylamine, etc.

The subject reaction steps (a) and (b) are performed at temperaturesbetween −70° C. and the boiling temperature of the solvent employed,preferably between −20° C. and +30° C. The reaction of step (b), betweenaniline having the general formula (V) and halosulfamoylurea having thegeneral formula (IV), may be conveniently performed without isolatingsaid halosulfamoylurea (IV), by adding the aniline (V) and the base(diluted with the same inert organic solvent used in the step (a) of theabove process), while operating in the same ambient in which the firstpassage was performed.

The heterocyclic amines having the general formula (II) and thehalosulfonylisocyanates having the general formula (III) are compoundsknown in the art.

The anilines having the general formula (V) can, if not already known ontheir own, be prepared according to the methods known in the art.

The compounds having the general formula (I), objects of this invention,have evidenced interesting biological activities and, in particular, ahigh herbicidal activity which renders them suitable for use in theagricultural field to defend the useful cultures from weeds.

In particular, the compounds having the general formula (I) areeffective in controlling, both before and after an emergency, numerouscotyledon and dicotyledon weeds. At the same time, these compounds showa compatibility or absence of toxic effects toward useful cultures, bothwhile treating before and after emergence.

Examples of weeds effectively controlled by using the compounds havingthe general formula (I) as the object of this invention are: Abutilontheofrasti, Amaranthus retroflexus, Amni maius, Capsella bursa pastoris,Chenopodium Album, Convolvulus sepium, Galium Aparine, Geraniumdicotomiflorum, Ipomea spp., Matricaria spp, Papaver rhoeas, Portulacaoleracea, Sida spinosa, Solanum nigrum, Stellaria media, Alopecurusmyosuroides, Digitaria sanguinalis, Echinocloa spp., Scirpus spp.,Cyperus spp., etc.

At the usage dosages useful for agricultural applications, the abovecompounds have not evidenced toxic effects towards importantagricultural cultures such as rice (Oryza sativa), wheat (Triticumspp.), corn (Zea mais), soya (Glycine max), etc.

A further object of this invention is a method to control weeds incultured areas, by applying the compounds having the general formula(I).

The quantity of a compound needed to achieve the desired result may varydepending on a number of factors such as, for instance, the compound tobe used, the culture to be preserved, the weed to be attacked, thedegree of infestation, the weather conditions, the characteristics ofthe soil, the method of application, etc.

Dosages of the compound in the range from 1 g to 1,000 g per hectaregenerally provide adequate control.

For practical applications in agriculture it is often beneficial toutilize compositions with a herbicidal activity containing, as an activesubstance, one or more compounds of the general formula (I), eventuallyalso in a mixture with isomers, both in a free or in a salified form.

It is possible to use compounds presenting themselves in the form of drypowders, wettable powders, emulsifyable concentrates, microemulsions,pastes, granulates, solutions, suspensions, etc.: the choice of the typeof composition will depend on the specific application.

The compositions are prepared according to known methods, for example bydiluting or solving the active substance in a solvent and/or solidmedium, eventually in the presence of surfactants.

The substances to be used as solid inert diluents or supports may becaoline, alumina, silica, talc, bentonite, gypsum, quartz, dolomite,attapulgite, montmorillonite, diatomaceous earth, cellulose, starch,etc.

The substances to be used as inert liquid diluents may, in addition towater, be organic solvents such as aromatic hydrocarbons (xylene, blendsof alkylbenzenes, etc.), aliphatic hydrocarbons (hexane, cyclohexane,etc.), aromatic halogenated hydrocarbons (chlorobenzene, etc.), alcohols(methanol, propanol, butanol, octanol, etc.) esters (isobutylacetate,etc.), ketones (acetone, cyclohexanone, acetophenone, isoforone,ethylamylketone, etc.), vegetable and mineral oils and their mixtures,etc.

As surfactants certain wetting and emulsifying agents may be used havinga non-ionic character (polyethoxylated alkylphenols, polyethxylatedfatty alcohols, etc.), an anionic character (alkylbenzenesulfonates,alkylsulfonates,etc.), a cationic character quaternary alkylammoniumsalts, etc.).

It may also be possible to add dispersants (for example lignin and itssalts, cellulose derivatives, alginates, etc.), stabilizers (for exampleantioxidants, ultraviolet ray absorbers, etc.).

To increase the range of action of the above compositions, other activeingredients can also be added such as, for example, other herbicides,fungicides, insecticides or acaricides, and fertilizers. Examples ofother herbicides which can be added to the compositions containing oneor more compounds of the general formula (I) are the following:

Acetochlor, acifluorfen, aclonifen, AKH-7088, alachlor, alloxydim,ametryn, amidosulfuron, amicrole, anilofos, asulam, atrazine, azafenidin(DPX-R6447), azimsulfuron (DPX-A8947), aziprotrine, benazolin,benfluralin, benfuresate, bensulfuron, bensulide, bentazone, benzofenap,benzthiazuron, bifenox, bilanafos, bispyribac-sodium (KIH-2023),bromacil, bromobutide, bromofenoxim, bromoxynil, butachlor, butamiphos,butenachlor, butralin, butroxydim, butylate, cafenstrole (CH-900),carbetamide, carfentrazone-ethyl (F-8426), chloromethoxyfen, chloramben,chlorbromuron, chlorbufam, chlorfurenol, chloridazon, chlorimuron,chlornitrofen, chlorotoluron, chloroxuron, chlorpropham, chlorsulforon,chlorthal, chlorthiamid, cinidon ethyl, cinmethylin, cinosulfuron,clethodim, chlodinafop, clomazone, clomeprop, clopyralid,chloransulam-methyl (XDE-565), cumyluron (JC-940), cyanazine, cycloate,cyclosulfamuron, (AC-322140), cycloxydim, cyhalofop-butyl (XDE-537),2,4-D, 2,4-DB, daimuron, dalapon, desnedipham, desmetryn, dicamba,dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclosulam (XDE-564),diethatyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr (SAN835H), dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dinitramine, dinoseb, dinoseb acetate, dinotherb,diphenamid, dipropetryn, diquat, dithiopyr, 1-diuron, eglinazine,endothal, epoprodan (MK-243), EPTC, esprocarb, ethalfluralin,ethametsulfuron-methyl (DPX-A7881), ethidimuron, ethiozin (SMY 1500),ethofumesate, ethoxyfen-ethyl (HC-252), ethoxysulfuron (HOE 095404),ethobenzanid (HW 52), fenoxaprop, fenoxaprop-P, fentrazamide (BAY YRC2388), fenuron, flamprop, flamprop-M, flazasulfuron, fluazifop,fluazifop-P, fluchloralin, flumetsulam (DE-498), flumiclorac-pentyl,flumioxazin, flumipropin, flumeturon, fluoroglycofen, fluoronitrofen,flupoxam, flupropanate, flupyrsulfuron (DPX-KE459), flurenol, fluridone,flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl (KIH-9201),fluthiamide (BAY FOE 5043), fomesafen, fosamine, furyloxyfen,glufosinate, glyphosate, halosulfuron-methyl (NC-319), haloxyfop,haloxyphop-P-methyl, hexazinone, imazamethabenz, imazamox (AC-299263),imazapic (AC-263222), imazapyr, amazaquin, imazethapyr, imazosulfuron,ioxynil, isopropalin, isopropazol (JV 485), isoproturon, isouron,isoxaben, isoxaflutole (RPA 201772), isoxapyrifop, KPP-421, lactofen,lenacil, linuron, LS830556, MCPA, MCPA-thioethyl, MCPB, mecoprop,mecoprop-P, mefenacet, metamitron, metazachlor, methabenzthiazuron,methazole, methoprotryne, methyldymron, metobenzuron, metobromuron,metolachlor, metosulam (DE-511), metoxuron, metribuzin, metsulfuron,molinate, monalide, monolinuron, naproanilide, napropamide, naptalam,NC-330, neburon, nicosulfuron, nipyraclofen, norflurazon, orbencarb,oryzalin, oxadiargyl, oxadiazon, oxasulfuron (CGA-277476),oxaziclomefone (MY-100), oxyfluorfen, paraquat, pebulate, pendimethalin,pentanochlor, pentoxazone (KPP-314), phenmedipham, picloram, piperophos,prenilachlor, primisulfuron, prodiamine, proglinazine, prometon,prometryne, propachlor, propanil, propaquizafop, propazine, propham,propisochlor, propyzamide, prosulfocarb, prosulfuron (CGA-152005),pyraflufen-ethyl (ET-751), pyrazolynate, pyrazolsulfuron, pyrazoxyfen,pyribenzoxim (LGC-40863), pyributicarb, pyridate, pyriminobac-methyl(KIH-6127), pyrithiobac-sodium (KIH-2031), quinchlorac, quinmerac,quizalofop, quizalofop-P, rimasulfuron, sethoxydim, siduron, simazine,simetryn, sulcotrione, sulfentrazone (F6285), sulfometuron (DPX-5648,sulfosulfuron (MON 37500), 2,3,6-TBA, TCA-sodium, tebutam, tebuthiuron,tepraloxydim (BAS 620H), terbacil, terbumeton, terbuthyl-azine,terbutryn, therylchlor (NSK-850, thiazafluron, thiazopyr (MON 13200),thidiazimin, thifensulfuron, thioencarb, tiocarbazil, tioclorim,tralkoxydim, tri-allate, triasulfuron (CGA-131036), triaxiflam(IDH-1105), tribenuron, triclopyr, trietazine, trifluralin,triflusilfuron-methyl (DPX-66037), UBI-C4874, vernolate.

The concentration of active substance of the general formula (I) in theabove compositions can vary within a wide range, depending on the activecompound, the applications for which they are destined, theenvironmental conditions and the kind of formulation. The

concentration of active substance is generally between 1% and 90%,preferably between 5 and 50%.

The following examples are illustrative and do not limit the scope ofthis invention.

EXAMPLE 1 Preparation of2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N,N-dimethylbenzamide(CompoundNr.1)

Under a nitrogen atmosphere, chlorosulfonyl isocyanate (4.3 g; 30.5mmoles) dissolved in methylene chloride (10 ml) are dropped into asolution of 2-amino-4,6-dimethoxypyrimidine (5.2 g; 33.6 mmoles) inmethylene chloride (50 ml) at −5° C.

The mixture is stirred at 0° C. for 1 h. A solution of2-amino-N,N-dimethylbenzamide (5 g; 30.5 mmoles) and triethylamine (3.1g; 30.6 mmoles) in methylene chloride (20 ml) is then added and themixture is stirred for 30 min at 0° C. and for further 3 hours at roomtemperature. The reaction mixture is poured into a 2 l. solution ofbrine and 1% aqueous HCl and extracted with methylene chloride. Theorganic phase is washed with brine, dried with sodium sulfate andconcentrated at reduced pressure. The residue (12.8 g) is stirred at 50°C. with ethyl acetate (20 ml); after cooling the solid is filtered andwashed with diethyl ether. The desired product (11.3 g) has a meltingpoint at 160-162° C.

EXAMPLE 2

Operating analogously to what is described in example 1, the followingcompounds have been prepared, starting from the appropriate2-aminopyrimidines and 2-aminobenzamides:

1-(4,6-dimethoxypyrimidin-2-yl)-3-{[2-(1-pyrrolidinocarbonyl)phenyl]sulfa-moyl}urea(Compound Nr. 2): m.p. 154-1560° C.;

2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-ethyl-N-methylbenzamide(Compound Nr. 3): m.p. 136-138° C.;

2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-methylbenzamide(Compound Nr. 4): m.p. 98-100° C.;

2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-ethylbenzamide(Compound Nr. 5): m.p. 98-100° C.;

2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-methoxybenzamide(Compound Nr. 6): m.p. 147-149° C.;

2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-methoxy-N-methylbenzamide(Compound Nr. 7): m.p. 137-139° C.;

2-(4,6-dimethoxypyrimidin-2-yl) carbamoylsulfamoylamino]benzamide(Compound Nr. 8): m.p. 164-166° C.;

2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylmethylamino]-N,N-dimethylbenzamide (Compound Nr. 9):m.p. 120-121° C.;

N-cyclopropyl-2-(4,6-dimethoxypyrimidin-2-yl) carbamoylsulfamoylamino)benzamide (Compound Nr. 10)-2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-(2,2,2-trifluoroethyl)-benzamide(Compound Nr. 11) -4-chloro-6-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N,N-dimethylbenzamide (Compound Nr. 12): m.p.161-163° C.;

3-chloro-6-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N,N-dimethylbenzamide (Compound Nr. 13): m.p.156-158° C.;

2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-5-fluoro-N,N-dimethylbenzamide (Compound Nr.14): m.p. 171-173° C.;

2-(4,6-dimethoxypyrimidin-2-yl)carbamoyisulfamoylamino]-6-fluoro-N,N-dimethylbenzamide (Compound Nr.15): m.p. 165-167° C.;

2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]5-methyl-N,N-dimethylbenzamide(Compound Nr. 16): m.p. 164-166° C.;

2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-6-methyl-N,N-dimethylbenzamide (Compound Nr.17): m.p. 169-171° C.;

N,N-dimethyl-2-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoylsulfamoylamino]-benzamide(Compound Nr. 18): m.p. 147-149° C.;

N,N-dimethyl-2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoylamino]-benzamide (Compound Nr. 19):

m.p. 163-165° C.

EXAMPLE 3 Preparation of2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylami-no]-N,N-dimethylbenzamidemonosodium salt (Compound Nr.20)

Crushed sodium hydroxide (400 mg; 10 mmoles) is added to a solution ofCompound Nr.1 (Example 1; 4.25 g; 10 mmoles) in 100 ml ofdichloromethane.

The mixture is stirred at room temperature for 18 h and concentratedunder reduced pressure. The solid residue (4.3 g) has a melting point at190° C.

EXAMPLE 4 Determination of the Herbicidal Activity and Phytotoxicity.

The herbicidal activity of Compounds Nr. 1, 2 and 4 with respect to someimportant weeds and the phytotoxicity with respect to wheat wereevaluated, in post-emergence treatment, compared to1-[(4,6-dimethoxypyrimidin-2-yl)-3-[(2-methoxycarbonylphenyl)sulfamoyl]ureadescribed in the example 2 of the US-patent 4,515,620 (RC).

For each compound, the evaluation tests were carried out according tothe following operating procedures.

Jars (diameter 10 cm, height 10 cm) containing sandy earth wereprepared. In each of them, one of the following plant species was sown:

Weeds: Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE),Amni maius (MNMA), Convolvulus sepium (CONSE), Galium Aparine (GALAP),Ipomea Purpurea (IPOPU), Papaver rhoeas (PAPRH), Solanum nigrum (SOLNI);

Crops: Triticum sp. (Wheat).

To each jar, water was added in a suitable amount for a good germinationof the seeds. The jars were divided into two groups each containing atleast 5 jars for each weed. The first group was not treated with thecompound under evaluation and was used as a comparison (control).

The second group of jars was treated, 15 days after sowing for the weedsand 10 days after sowing for wheat, with a hydroacetonic dispersion (20%by volume of acetone) containing the compound under testing at thedesired rate and Tween 20 (0.5%).

All jars were kept under observation in a conditioned environment withthe following conditions:

temperature: 24° C.

relative humidity: 60%

photoperiod: 16 hours

light intensity: 10,000 lux

Every two days the jars were uniformly watered to ensure a sufficientdegree of humidity for a good development of the plants.

Twentyone days after the treatment, the herbicidal activity wasevaluated on the basis of the following scale of values referring to thepercentage of damage found on the plants which had been treated,compared to those not treated (control):

0=0%-9% of damage

1=10%-29% of damage

2=30%-49% of damage

3=50%-69% of damage

4=70%-89% of damage

5=90% of damage—death of plant

The results obtained are as shown in Table 1 below.

TABLE 1 Herbicidal activity in post-emergence Nr.2 Nr.4 RC COMPOUND Nr.1150- 150- 150- WEED/CROP Rate (g/ha) 150-50 50 50 50 ABUTH 5-3 4-2 5-35-2 AMARE 5-3 1-0 5-4 3-1 AMNMA 4-3 4-3 5-4 2-1 CONSE 5-5 5-5 5-nt 3-1GALAP 5-3 4-1 5-4 4-2 IPOPU 5-3 nt-nt 5-4 nt-0 PAPRH 5-4 5-4 nt-nt nt-0SOLNI 5-3 3-2 nt-nt nt-0 WHEAT 0-0 0-0 0-0 0-0 nt = not tested.

What is claimed is:
 1. A compound having the formula (I):

in which: R represents a halogen atom; and alkyl or haloalkyl linear orbranched C₁-C₄ group; and alkoxy or haloalkoxy linear or branched C₁-C₄group; n represents 0 or 1; R₁ and R₂, equal or different from eachother, represent hydrogen; and alkyl or haloalkyl linear or branchedC₁-C₄ group; and alkoxy or haloalkoxy linear or branched C₁-C₄ group; orjointly an alkenyl or oxyalkenyl chain C₂-C₅; R₃ and R₄, equal ordifferent from each other, represent hydrogen; and alkyl or haloalkyllinear or branched C₁-C₄ group; and alkoxy or haloalkoxy linear orbranched C₃-C₆ group; and alkenyl or haloalkenyl linear or branchedC₃-C₆ group; and alkynyl or haloalkynyl linear or branched C₃-C₆ group;R₅ and R₆, equal or different from each other, represent hydrogen;halogen; and alkyl or haloalkyl linear or branched C₁-C₆ group; andalkylamino linear or branched C₁-C₆ group; a dialkylamino linear orbranched C₂-C₈ group; a cycloalkyl or cycloalkoxy C₃-C₆ group; acycloalkylalkyl or cycloalkylalkoxy C₄-C₇ group; Z represents—CH.
 2. Acompound according to claim 1 which is-2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N,N-dimethylbenzamide.3. A compound according to claim 1 which is-1-(4,6-dimethoxypyrimidin-2-yl)-3{[2-(1-pyrrolidinocarbonyl)phenyl]sulfamoyl}urea.4. A compound according to claim 1 which is-2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-methylbenzamide.5. A compound according to claim 1 which is-2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-ethylbenzamide.6. A compound according to claim 1 which is-2-(4,6-dimethoxypyrimidin-2yl)carbamoylsulfamoylamino]-N-methoxybenzamide.7. A compound according to claim 1 which is-2-(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-methoxy-N-methylbenzamide.8. Alkali metal, alkaline earth metal, optionally alkylated ammonium ororganic amine salts of compound, according to claim 1.